Triphenylphosphine → Benzyl 2-[(pyridin-2-yl)oxy]propanoate

HRID 1394548

反応式

HRID 1394548 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:12])[CH:9]([CH3:11])O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl.CCCCCC>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH:9]([CH3:11])[C:8]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 98054Benzyl lactateHCID 5462977Diethyl azodicarboxylateHCID 178516071HCID 178516071、化合物

生成物 1

HCID 16098326Benzyl 2-[(pyridin-2-yl)oxy]propanoate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

To a mixture of 2-hydroxypyridine (2.9 g, 30 mmol), benzyl lactate (5.0 g, 21 mmol) and triphenylphosphine (12 g, 47 mmol) in 100 mL of methylene chloride was added diethylazodicarboxylate (7.8 mL, 45 mmol) at 0° C. The reaction was allowed to warm to room temperature for 4 h. The resulting mixture was diluted with hexane (100 mL) and concentrated with 20 g of silica gel. The material was loaded onto a silica gel column, which was eluted with 10% ethyl acetate in hexane to give the title compound. 1H NMR (500 MHz, CD3OD): δ 8.00 (dd, 1H), 7.68 (ddd, 1H), 7.36-7.28 (m, 5 H), 6.94 (dd, 1H), 6.84 (dd, 1H), 5.30 (q, 1H), 5.18 (s, 2H), 1.59 (d, 3H). LC-MS: m/e 258 (M+H)+ (3.3 min).

後処理

  1. concentrationconcentrated with 20 g of silica gel
  2. washwas eluted with 10% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-6d0fa835ff6b4a0393ff26662fa4ca7e
出典データセット
uspto-grants-2008_03
特許番号
US07348456B2

関連ノート

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